What is the cheapest airline that flies from Chicago Midway to Milan?

KLM and Delta are the most popular carriers operating from Chicago Midway to Milan

When did momondo last update prices for flights from Chicago Midway Airport to Milan?

Prices for flights from Chicago Midway Airport to Milan are updated daily.

How old do you have to be to fly from Chicago Midway Airport to Milan?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

What documentation or ID do you need to fly to Milan?

The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$325 Cheap Flights from Chicago Midway Airport to Milan in 2025/26

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One-way

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12:47 pm - 8:05 am

MDW

MXP

13h 18m1 stop

11:40 am - 10:29 pm

MXP

MDW

17h 49m1 stop

$975KLM

Mon, Mar 23 - Tue, Apr 7

6:34 pm - 2:55 pm

MDW

MXP

14h 21m2 stops

11:40 am - 10:31 pm

MXP

MDW

17h 51m1 stop

$979Delta

Mon, Mar 23 - Tue, Apr 7

10:53 am - 9:05 am

MDW

MXP

15h 12m1 stop

11:05 am - 10:31 pm

MXP

MDW

18h 26m1 stop

$1,030KLM

Thu, Feb 26 - Wed, Mar 4

9:33 am - 9:05 am

MDW

MXP

16h 32m2 stops

9:25 am - 10:31 pm

MXP

MDW

20h 06m2 stops

$1,034Delta

Tue, Feb 10 - Sun, Feb 15

1:10 pm - 10:00 am

MDW

LIN

14h 50m2 stops

6:30 am - 6:40 pm

LIN

MDW

18h 10m2 stops

$1,049Delta

Thu, Mar 12 - Tue, Mar 17

6:20 am - 9:05 am

MDW

MXP

19h 45m1 stop

11:05 am - 10:34 pm

MXP

MDW

18h 29m1 stop

$1,053Multiple Airlines

Thu, Feb 5 - Thu, Feb 12

9:34 am - 9:05 am

MDW

MXP

16h 31m2 stops

11:00 am - 10:31 pm

MXP

MDW

17h 31m2 stops

$1,059Delta

Thu, Mar 5 - Sat, Mar 21

10:46 am - 9:05 am

MDW

MXP

15h 19m1 stop

11:05 am - 10:22 pm

MXP

MDW

18h 17m1 stop

$1,080KLM

Wed, Jan 28 - Thu, Feb 5

1:26 pm - 11:40 am

MDW

MXP

15h 14m2 stops

11:05 am - 10:22 pm

MXP

MDW

18h 17m1 stop

$1,084Delta

Wed, Jan 28 - Wed, Feb 4

10:46 am - 9:45 am

MDW

MXP

15h 59m2 stops

6:25 pm - 5:29 pm

MXP

MDW

30h 04m2 stops

$1,107Multiple Airlines

Mon, Jan 19 - Mon, Jan 26

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets

Delta

Mar 10

MDW10:45 amChicago Midway

15h 20m

1 stop

MXP8:05 amMilan Malpensa

Mar 18

MXP10:05 amMilan Malpensa

18h 26m

1 stop

MDW10:31 pmChicago Midway

$830

Find similar

Delta

Feb 9

MDW1:26 pmChicago Midway

14h 09m

2 stops

MXP10:35 amMilan Malpensa

Feb 25

MXP11:05 amMilan Malpensa

18h 26m

1 stop

MDW10:31 pmChicago Midway

$834

Find similar

Delta

Mar 23

MDW6:34 pmChicago Midway

14h 21m

2 stops

MXP2:55 pmMilan Malpensa

Apr 7

MXP11:40 amMilan Malpensa

17h 51m

1 stop

MDW10:31 pmChicago Midway

$979

Find similar

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets

KLM

Feb 9

MDW10:46 amChicago Midway

15h 19m

1 stop

MXP9:05 amMilan Malpensa

Feb 25

MXP11:05 amMilan Malpensa

18h 26m

1 stop

MDW10:31 pmChicago Midway

$880

Find similar

KLM

Feb 9

MDW10:46 amChicago Midway

15h 19m

1 stop

MXP9:05 amMilan Malpensa

Feb 18

MXP11:05 amMilan Malpensa

18h 37m

1 stop

MDW10:42 pmChicago Midway

$889

Find similar

KLM

Mar 23

MDW12:47 pmChicago Midway

13h 18m

1 stop

MXP8:05 amMilan Malpensa

Apr 7

MXP11:40 amMilan Malpensa

17h 49m

1 stop

MDW10:29 pmChicago Midway

$975

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/23

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Tue 4/7

11:40 am-10:29 pm

1 stop17h 49m

$975

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/23

6:34 pm-2:55 pm

2 stops14h 21m

Milan Malpensa

Tue 4/7

11:40 am-10:31 pm

1 stop17h 51m

$979

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 2/26

10:53 am-9:05 am

1 stop15h 12m

Milan Malpensa

Wed 3/4

11:05 am-10:31 pm

1 stop18h 26m

$1,030

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 2/10

9:33 am-9:05 am

2 stops16h 32m

Milan Malpensa

Sun 2/15

9:25 am-10:31 pm

2 stops20h 06m

$1,034

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Thu 3/12

1:10 pm-10:00 am

2 stops14h 50m

Milan Linate

Tue 3/17

6:30 am-6:40 pm

2 stops18h 10m

$1,049

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 2/5

6:20 am-9:05 am

1 stop19h 45m

Milan Malpensa

Thu 2/12

11:05 am-10:34 pm

1 stop18h 29m

$1,053

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/5

9:34 am-9:05 am

2 stops16h 31m

Milan Malpensa

Sat 3/21

11:00 am-10:31 pm

2 stops17h 31m

$1,059

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 1/28

10:46 am-9:05 am

1 stop15h 19m

Milan Malpensa

Thu 2/5

11:05 am-10:22 pm

1 stop18h 17m

$1,080

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 1/28

1:26 pm-11:40 am

2 stops15h 14m

Milan Malpensa

Wed 2/4

11:05 am-10:22 pm

1 stop18h 17m

$1,084

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 1/19

10:46 am-9:45 am

2 stops15h 59m

Milan Malpensa

Mon 1/26

6:25 pm-5:29 pm

2 stops30h 04m

$1,107

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,183. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,485.

What is the cheapest time of day to depart on your flight to Milan?

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $1,349. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time	12h 21m
Direct flights	None

The fastest flight from Chicago Midway Airport to Milan takes 12h 21m

There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.

Search flight deals

How far is Chicago Midway to Milan by plane?
Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 12h 21m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Milan?
Prices for flights from Chicago Midway Airport to Milan are updated daily.
How old do you have to be to fly from Chicago Midway Airport to Milan?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.
What documentation or ID do you need to fly to Milan?
The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Bellagio

Varenna

Menaggio

Brescia

Stresa

Monza

Levanto

Assago

Livigno

Bellano

Lecco

Domodossola

Crema

Bormio

Rho

Cernobbio

Moltrasio

Saronno

Baveno

Novara

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

An easier way to manage your Milan trip

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Milan Linate Airport

Milan Malpensa Airport

Cheap flights from Chicago Midway Airport to Milan from $325

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 1/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,183. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,485.

What is the cheapest time of day to depart on your flight to Milan?

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

What is the cheapest airline that flies from Chicago Midway to Milan?

KLM and Delta are the most popular carriers operating from Chicago Midway to Milan

When to book flights from Chicago Midway Airport to Milan

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time

Direct flights

How far is Chicago Midway to Milan by plane?

When did momondo last update prices for flights from Chicago Midway Airport to Milan?

How old do you have to be to fly from Chicago Midway Airport to Milan?

What documentation or ID do you need to fly to Milan?

Traveling to a place near Milan?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Milan?

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

An easier way to manage your Milan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan